Polyaniline has attracted much attention in the field of organic conducting polymers due to its robust nature in the doped emeraldine state. See, for example, Huang et al. (1986) J. Chem. Soc. Faraday Trans. 82:2385-2400; Chen et al. (1991) Macromolecules 24:1242-1248; and Chiang et al. (1986) Synth. Met. 13:193-205. Among the many industrial applications it has found are its use as components in rechargeable batteries (MacDiarmid et al. (1986) Mol. Cryst. Liq. Cryst. 121:187-190), electromagnetic interference shielding (Taka et al. (1991) Synth. Met. 41:1177-1180; Colaneri et al. (1992) IEEE Trans. Instrum. Meas. 41:291; and Joo et al. (1994) Appl. Phys. Lett. 65:2278-2280), and anticorrosion coatings for steel (DeBerry et al. (1985) J. Electrochem. Soc. 132:1022-1026; Ahmad et al. (1996) Synth. Met. 78:103-110; and Lu et al. (1995) Synth. Met. 71:2163-2166).
In 1986, Wudl and coworkers demonstrated that synthetically prepared phenyl-capped octaaniline exhibited properties similar to bulk polyaniline (comparable UV/vis, IR, CV, and conductivity). See Lu et al. (1986) J. Am. Chem. Soc. 108:8311-8313; Wudl et al. (1987) J. Am. Chem. Soc. 109:3677-3684. Consequently, an octaaniline may be considered a good model or substitute for applications involving polyaniline. Aside from the modified Honzl condensation method employed by Wudl for synthesizing oligoanilines, other methods of preparation include titanium alkoxide-mediated couplings of aniline derivatives (Ochi et al. (1994) J. Bull. Chem. Soc. Jpn. 67:1749-1752), Ullmann couplings (Rebourt et al. (1997) Synth. Met. 84:65-66), and an adaptation of the Willstatter-Moore approach (Zhang et al. (1997) J. Synth. Met. 84:119-120). However, none of these methods have demonstrated generality in the choice of substrates for oligomerizations, and all lack the ability to functionalize end groups.